14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner

Make it your trip
Fly
1
Kailua-Kona, Island of Hawaii
— 1 night
Drive
2
Volcano, Island of Hawaii
— 2 nights
Fly
3
Lahaina, Maui
— 5 nights
Fly
4
Honolulu, Oahu
— 5 nights
Fly

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Kailua-Kona, Island of Hawaii

— 1 night

Heart of the Kona Coast

Thanks to its favorable location near a mountain range blocking the northeasterly trade winds, Kailua-Kona gets little rainfall, allowing adventure seekers and nature lovers a chance to enjoy over 300 days of sunshine each year.
Kick off your visit on the 6th (Mon): kick back and relax at Kahaluu Beach, experience rural life at Heavenly Hawaiian Kona Coffee Farm, then see some colorful creatures with a scuba or snorkeling tour, and finally contemplate in the serene atmosphere at Mokuaikaua Church.

To find maps, traveler tips, more things to do, and more tourist information, go to the Kailua-Kona trip builder.

Boston to Kailua-Kona is an approximately 15-hour flight. You'll gain 5 hours traveling from Boston to Kailua-Kona due to the time zone difference. Plan for a bit warmer temperatures traveling from Boston in September, with highs in Kailua-Kona at 87°F and lows at 76°F. Finish up your sightseeing early on the 6th (Mon) so you can go by car to Volcano.

Things to do in Kailua-Kona

Outdoors · Wildlife · Tours · Parks

Side Trips

Volcano, Island of Hawaii

— 2 nights
Those who named Volcano opted for simplicity in choosing a title, taking the nearby fire-spewing Kilauea as a source of inspiration.
Kick off your visit on the 7th (Tue): take in nature's colorful creations at Akatsuka Orchid Gardens, trek along Sulphur Banks, then see the interesting displays at Jagger Museum, then trek along Kilauea Iki Trailhead, and finally cruise along Devastation Trail. Get ready for a full day of sightseeing on the 8th (Wed): see the world from above with a helicopter tour, then take in nature's colorful creations at Liliuokalani Gardens, then take in the dramatic scenery at Rainbow Falls, and finally take in the dramatic scenery at Akaka Falls State Park.

For more things to do, traveler tips, reviews, and tourist information, use the Volcano trip itinerary app.

Traveling by car from Kailua-Kona to Volcano takes 2.5 hours. Alternatively, you can take a bus. Traveling from Kailua-Kona in September, you can expect nighttime temperatures to be slightly colder in Volcano, with lows of 71°F. Cap off your sightseeing on the 8th (Wed) early enough to catch the flight to Lahaina.

Things to do in Volcano

Parks · Outdoors · Trails · Nature

Side Trips

Lahaina, Maui

— 5 nights

Crown Jewel of Maui

Once the booming capital of the Hawaiian Kingdom, the tropical paradise of Lahaina still remains one of Maui's top vacation attractions, providing both culture and recreation.
Explore Lahaina's surroundings by going to Maui Veterans Cemetery (in Makawao) and Haleakala Crater (in Haleakala National Park). Spend the 10th (Fri) exploring the striking scenery along Hana Highway - Road to Hana. There's still lots to do: take a tour by water with Boat Tours & Water Sports, view the masterpieces at Lahaina Galleries, observe the fascinating underwater world at Maui Ocean Center, and experience rural life at Maui Nui Farm.

To find other places to visit, ratings, maps, and other tourist information, you can read our Lahaina itinerary tool.

Traveling by flight from Volcano to Lahaina takes 2.5 hours. In September, daytime highs in Lahaina are 86°F, while nighttime lows are 74°F. Wrap up your sightseeing on the 13th (Mon) early enough to fly to Honolulu.

Things to do in Lahaina

Parks · Outdoors · Scenic Drive · Beaches

Side Trips

Honolulu, Oahu

— 5 nights

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Venture out of the city with trips to Pu’u O Mahuka Heiau State Monument (in Pupukea), Kailua Beach Park (in Kailua) and Haleiwa (Waimea Bay & Sunset Beach Park). And it doesn't end there: explore the different monuments and memorials at USS Arizona Memorial, explore the galleries of Iolani Palace, take a tour by water with Boat Tours & Water Sports, and stroll around Kapiolani Regional Park.

To see other places to visit, traveler tips, photos, and other tourist information, refer to the Honolulu trip planner.

You can fly from Lahaina to Honolulu in 2.5 hours. In September, plan for daily highs up to 88°F, and evening lows to 76°F. Wrap up your sightseeing on the 18th (Sat) early enough to fly back home.

Things to do in Honolulu

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Hawaii travel guide

4.4
Scuba & Snorkeling · Beaches · Zipline
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.